Things and OmniFocus

So. I’m anticipating that 2019 will be very busy for me, and I’ve been thinking that I may need a more robust method for tracking all of my tasks.

I never seriously considered any other options besides OmniFocus and Things. I briefly examined TickTick, 2Do, and Any.do, and I think one or two others, but — for no good reason — they were never really in the running.

And let me get the big question out of the way right here: I chose OmniFocus.

daily to-do lists and braindumps in a Field Notes notebook that’s always always always with me.

I do not expect a task manager to replace any of that. I will never give up the tactile pleasure of using a pen to cross something off a list written on a piece of paper. And I probably I won’t be using Due nearly as often, but I know I’ll always have little isolated to-do’s that I need to be nagged about, and Due is better suited to that. And yes, it makes perfect sense for me to view my calendar events within a task manager, but a calendar app is not a task manager, and a task manager is not a calendar app.

I do not believe that any one app can — or should — be all things to everyone. There are things that are out of scope for task managers. Indeed, there are things that are out of scope for computers.

Tools help you think; they can’t think for you. They can help you make decisions; they can’t decide for you. A car doesn’t know where you want to go; a roadmap doesn’t know how you want to get there. But if they are well-designed, they will get out of the way of the journey once you choose your destination.

Also, I wasn’t coming from a different task manager app; I’ve never used anything like OmniFocus, Things, 2Do, etc. I’ve worked inside environments like Asana, Basecamp, Active.Collab, Evernote, Trello, Igloo, and Quip, but those are all project management systems, of which task management is a subset.

Therefore, I didn’t have very many preconceived notions of how a task manager should function. So rather than comparing OmniFocus and Things to any of these other apps, I was comparing them to how I already work. And, of course, I was comparing them to each other.

(Oh, and I should add that going into this evaluation period, I was only vaguely familiar wth the basics of the GTD method. I only mention this because I’d heard that Things in particular was designed with GTD in mind.)

Now, then.

I tend to plan ahead rather obsessively. So I’d barely launched Things and OmniFocus for the first time and I had already generated many pages of notes: lists of potential tags and projects, needs and preferences; sample to-do’s and the various ways to describe them. I asked myself: what’s the difference between a tag and a project? an action and a deadline? recurring items and repeating items? is “Work” a project, or a type of project? And so on. I looked at my paper to-do lists and at Due to see what I already do. I thought about what I expect from a task manager, and what I don’t expect. I thought about what I already find easy and what I still find difficult about managing all the tasks in my life.

In short, I examined how I know I already work, and tried to describe it all to myself.

My answers will, of course, be very different from anyone else’s. And the fact that I asked any of those questions in the first place marks me out as a particular sort of person. I think it’s perfectly possible to launch either Things or OmniFocus without any of this soul-searching and still simply get to work. But sooner or later, everyone needs to ask themselves at least some of these questions, or else they may find themselves rearranging their workspace during a project instead of beforehand.

(You don’t have to make a million lists and ponder endlessly like I do, but at the very least, take a little time at the beginning to set your workspace. After all, you always have more time than you think.)

After clicking around in Things and OmniFocus, checking the preference panes, adding random dummy to-do’s, I then set up an identical project in each of them. I compared their data-entry methods, and looked at how similarly and differently each app described a typical to-do. And when I entered a to-do via the several different input methods, where did it go? and how easily could I find it again? How much nagging could I get the apps to do, and how easily could I tell them to shut up?

Here’s what I discovered.

I could make OmniFocus work like Things, but I had a hard time making Things work like OmniFocus.

There are, of course, many different ways to think about time, and about actions, and about projects. If you already think the way Things encourages you to, then you will probably prefer Things. If you think in any other sort of way, you’ll probably prefer OmniFocus.

In a word: Things struck me as prescriptive, and OmniFocus descriptive.

Now, all this is fine. I absolutely don’t think this makes Things an inferior product. It just means Things has a more forceful personality; it’s more opinionated on how humans should get things done. It’s prescriptive.

And honestly? I might have been perfectly content — and even delighted — to work in Things, despite the misgivings I have about its lack of community support, the relative youth of the company (compared to the venerable Omni Group), and that troubling window of time recently when development seemed to just stall for a few years. After all, Things is absolutely lovely, and has many stunning and clever features.

But when I was evaluating these apps, I wasn’t just thinking about myself and my own needs; I was also considering my wife, who’s also my business partner, and how I know she works. She’s been an administrative and executive assistant since she was a teenager; she’s been an executive coach, and she trains individuals and teams in process and project management. And I knew she would never be able to adapt Things to her needs. It would have been a battle of wills between them, and who needs that sort of grief?

I gave myself a crash-course in GTD earlier this week, and I can see now that Things’ prescriptiveness almost certainly comes from its allegience to GTD. Fair enough. It’s a good system. (If my praise seems faint, it’s only because I’d rather mull on it for a few more months before saying anything else.)

So. If you follow the GTD method closely — or if you haven’t already developed your own strong and time-tested method for task management — then I would enthusiastically recommend Things.

And if you have that peculiarly modern condition I call Preferences ADD — that is, if you’re inclined to obsess over and get distracted by all the fiddly bits, if you continuously revisit, re-litigate, rearrange your workspace just cuz, then you may find OmniFocus just too open. Better stick with Things: it knows what you should be doing.

But if you’re like me (and I know I am), and you already have a system, then you might be happier with OmniFocus, if only because it seems far more flexible, far more agnostic. It wants you to be yourself, just a little better and a little more organized.

Tools help you think; they can’t think for you. What type of tool do you need to help you think?